5 Mistakes I’ve Made In My Calligraphy Business

You guys already know I love to talk about business, and while I try to focus on the positive/educational side of things, I think it’s just as important to talk about the trial & error that we all go through on our business journeys. Most of what I know about business, truly, has come from making lots - and lots - of mistakes.

This has been me way more times than I would like to admit.

This has been me way more times than I would like to admit.

In honour of the exciting new online course that I created with Sylvia Wong of Via Calligraphy, (which is called The Badass Brand Academy, and is all about helping other creatives avoid these growing pains and get on the fast track to successful business babe life) - I thought I would share some of the mistakes that I’ve made in my own business. So here we go…

5 Mistakes I made in my Calligraphy Business

1. Spending too much time on the wrong tasks.

When I think back to how much time I wasted “perfecting” my website - tweaking the colours, agonizing over the fonts, switching templates 18 times - I honestly shudder. I was so consumed by the aesthetic aspect (which is important, don’t get me wrong, but not something you should spend 80 hours on - especially when you haven’t made any money yet!) that I completely ignored the things that would have actually made a difference to my business right away. Things like SEO, creating engaging content & blog posts, building an e-mail list, and crafting the message behind my brand. If I could go back in time, I would have learned everything I could about all those things first, slapped together a website in a day, and worried about the aesthetics later!

2. Being too shy to enforce my own policies.

Now that I’m a weathered old bat/cold-hearted business bitch (I mean…not really. But kind of.) I almost never make this mistake anymore. Sadly I do still catch myself letting small things slide that I know I shouldn’t. Being more assertive is something I’m always working on, because I do worry about being perceived as difficult or demanding. However in the early days, I was so shy that I would borderline not even ask to be paid. I would do work without a deposit, or without a contract, I would run around town delivering signage without charging for my time, I would wait around for weeks for an invoice to be paid and not make a peep. I allowed myself to be walked all over time and time again. Eventually I decided enough was enough, and now I hardly ever waver from my policies (which are fairly strict - ex. A late fee of 5% of the total project cost is charged per day that an invoice is late). But I do wish that there had been someone there to take my face in their hands and give me a sassy pep talk - I would have avoided many crying-into-a-tub-of-ice-cream moments (…and I probably would have made a ton of money on late fees. Going back to my Blockbuster roots, y’know?)

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3. Pretending that money didn’t matter.

I got into this whole calligraphy biz thing because I am an artist at heart - not a business-person. I just truly want to create beautiful things, and I genuinely never expected to make more than a mostly-adequate living from art. I used to think I would just be grateful to be able to pay my bills doing what I loved, and wanting anything more than that was somehow wrong, or greedy. That is, after all, kind of the narrative that’s out there for a lot of artists. I felt like there was a pretty low ceiling to how much I could ever make. After a while though, I realized that I have just as much of a right to make a comfortable living as anyone else in any other field. That I shouldn’t hold myself back because of societal expectations, or outdated concepts like the “Starving Artist”. It took time and a lot of un-learning of ingrained ideas, but I gradually shifted my money mindset, and made my finances a top priority instead of an afterthought.

4. Thinking that Saying No was a bad thing.

Guys. Saying “No” is basically my new favourite thing. I used to say yes to every project & every client, thinking it made me innovative and bold to always be trying new things, even if I wasn’t completely sure I knew how. When I first left my full-time job, I also felt like I wasn’t in a position to turn down work, so that led to a lot of projects I had absolutely no business taking on. There’s always a little spark of excitement when someone contacts you for a job - and then another feeling when you read the description of that job: either more excitement…or a pang of dread. I would say yes either way. Until one day, I got an email for something completely out of my wheelhouse - someone who was opening a restaurant, and wanted a full sign painted on the outdoor awning of their new establishment, in a vintage serif lettering style. I furiously googled sign-painting, trying to convince myself I could figure it out, and then I stumbled upon the website of Mr.Sign - another Montreal lettering artist who specializes in restaurant signage. And it occurred to me…I could just refer the client to him. He actually knows how to do this. So I did, and a huge wave of relief passed through me as I pressed “send” on that e-mail. Turns out, the feeling of liberation when saying “No” to something you either don’t know how, or don’t want to do - well, it’s fucking fabulous.

5. Trying to go it alone.

As someone who works alone at home all day, I have had a lot of one-sided conversations with my dog. And as much as he is an adorable angel who supports and loves me unconditionally, he can’t really give me any feedback when I have a situation or an idea that I need help working through. That’s why I’m extremely happy that I finally have an amazing group of fellow boss babes who I regularly talk to, bounce ideas off of, and occasionally ask to talk me off a ledge for one reason or another. I enjoy being independent, and as an introvert - I love my alone time - but it’s really lovely to have somewhere to turn when you need valuable advice or a second opinion. Being self employed can be isolating, and it’s super important to have a supportive network that you can rely on. You absolutely don’t have to go it alone, and you shouldn’t! It’s a lot better for your sanity to surround yourself with like-minded creatives when you need it.

So, those are 5 of the many mistakes that I made when in the early days of calligraphy business. Thankfully I learned from each of them, and they’re the reason I was able to change and grow my business. If you enjoyed this post, it would mean the world to me if you would share the below image on Pinterest, so more people can learn what not to do!

If you’re in the market for a business road-map that will help you break through your self doubt and turn your hobby into a high end business, Syl and I created the perfect online for you! Check out The Badass Brand Academy here - Enrollment is currently closed, but grab a spot on the waitlist to be notified when the next semester starts!


PSSST…Speaking of Business - if you’re in the market for a way to majorly streamline and organize your biz, I happen to have a gorgeous little 50% off discount for Honeybook! Give it a try for free and if you love it (I promise you will) the discount is all yours.